| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
CYP4A2 (IC50: 22 uM), CYP4A3 (IC50: 6.5 uM), CYP2C9, cyclooxygenase (COX)
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|---|---|
| ln Vitro |
When a 30-minute NADPH pre-incubation is present, PPOH (5 μM) can suppress CYP2C9 activity by 63% and 90%, respectively, and by 63% when NADPH is not included in the 30-minute pre-incubation [1].
PPOH is a fatty acid analog that selectively inhibits arachidonate epoxygenation. It inhibits CYP4A2 with an IC50 of 22 uM and CYP4A3 with an IC50 of 6.5 uM. It inhibits the reaction of epoxide formation (IC50 of 90 uM) at arachidonate positions 11 and 12 by CYP4A2 and CYP4A3 isozymes. With a 30-minute NADPH pre-incubation, PPOH (5 uM) can suppress CYP2C9 activity by 63% and 90%, respectively, and by 63% when NADPH is not included in the 30-minute pre-incubation. It is also a selective cyclooxygenase (COX) inhibitor that inhibits arachidonic acid cyclooxygenase activity in renal cortical microsomes. PPOH does not inhibit other arachidonate-metabolizing enzymes. |
| ln Vivo |
No specific in vivo data for PPOH. As an inhibitor of CYP epoxygenases, PPOH would be expected to alter the production of epoxyeicosatrienoic acids (EETs) from arachidonic acid in vivo, with potential effects on renal and cardiovascular function. In vivo studies would involve administration to rodents (e.g., intraperitoneal injection or oral gavage) at doses of 1-50 mg/kg, followed by measurement of EET levels in plasma or tissues (by LC-MS/MS), and assessment of blood pressure, renal function, or vascular reactivity. However, published in vivo studies are not readily available.
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| Enzyme Assay |
Recombinant human CYP4A2, CYP4A3, CYP2C9, or other CYP isoforms are expressed in E. coli or insect cells and reconstituted with NADPH-cytochrome P450 reductase. The enzyme activity assay measures the conversion of arachidonic acid (10-100 uM) to epoxyeicosatrienoic acids (EETs: 5,6-EET, 8,9-EET, 11,12-EET, 14,15-EET) and other metabolites. Reactions are incubated at 37degC for 10-30 minutes in a buffer containing potassium phosphate (pH 7.4), MgCl2, and an NADPH-regenerating system. The reaction is stopped by acidification and organic extraction. Products are separated by reverse-phase HPLC and quantified by UV absorbance at 210 nm or by LC-MS/MS. IC50 values are determined from dose-response curves. For the cyclooxygenase (COX) activity assay, the same protocol is used but product separation and quantification focus on prostaglandins.
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| Cell Assay |
Human renal cortical microsomes or other tissue microsomes are used for COX and CYP epoxidase assays. Microsomes are incubated with PPOH (0.1-100 uM) in the presence of arachidonic acid (10-100 uM) and an NADPH-regenerating system (for CYP enzymes) or with arachidonic acid alone (for COX). For cell-based assays, primary human renal cells, endothelial cells, or CYP-overexpressing cell lines (e.g., HEK293-CYP4A2) are cultured in appropriate media. Cells are treated with PPOH (0.1-100 uM) for 1-24 hours, then arachidonic acid (10-50 uM) is added. EETs and other metabolites in the culture supernatant are extracted and quantified by LC-MS/MS. Cell viability is assessed by MTT or LDH assays. The effects of PPOH on arachidonic acid metabolism and downstream signaling (e.g., MAPK, NF-kappaB) can be assessed by Western blot.
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| Animal Protocol |
No published in vivo animal study for PPOH. A typical protocol for assessing CYP epoxygenase inhibition in vivo would involve administering PPOH to male Sprague-Dawley rats or C57BL/6 mice via intraperitoneal injection (e.g., 10 mg/kg in a suitable vehicle such as saline with 5% DMSO or 10% PEG400). Blood and urine samples are collected at various time points (0-24 hours). Arachidonic acid metabolites (EETs, dihydroxyeicosatrienoic acids (DHETs), prostaglandins) are extracted from plasma, urine, or tissues (kidney, liver, heart) and quantified by LC-MS/MS. Blood pressure (by tail-cuff or telemetry), renal function (serum creatinine, BUN), and oxidative stress markers (MDA, 8-isoprostane) are measured. However, such studies are not widely reported.
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| ADME/Pharmacokinetics |
No specific pharmacokinetic data for PPOH. As a synthetic fatty acid analog (molecular weight 246.3, C15H18O3), it is likely to be highly plasma protein bound and distribute to lipid-rich tissues. PPOH is expected to be rapidly absorbed after intraperitoneal administration. It is metabolized by beta-oxidation and CYP enzymes, but specific metabolic pathways are not described. PPOH contains an alkyne group, which can be metabolized by CYP enzymes and may cause mechanism-based inhibition. Pharmacokinetic parameters (half-life, Cmax, AUC, clearance, bioavailability) are not publicly available.
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| Toxicity/Toxicokinetics |
No specific toxicity data for PPOH. As an inhibitor of CYP epoxygenases and COX, PPOH may alter arachidonic acid metabolism, which is involved in many physiological processes (renal function, vascular tone, inflammation, platelet aggregation). Potential toxicities could include hypertension, renal impairment, gastrointestinal irritation, and bleeding risk. Long-term safety studies are not available. PPOH is a click chemistry reagent and should be handled with standard laboratory safety precautions. Not for human use.
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| References | |
| Additional Infomation |
PPOH is an aromatic ether.
PPOH (CAS: 206052-01-9) is a research tool for studying arachidonic acid metabolism, specifically the epoxygenase pathway mediated by CYP4A and CYP2C enzymes, as well as the cyclooxygenase (COX) pathway. It is used to investigate the roles of epoxyeicosatrienoic acids (EETs) in renal, cardiovascular, and inflammatory biology. PPOH contains an alkyne group, which makes it a click chemistry reagent for copper-catalyzed azide-alkyne cycloaddition (CuAAC) with azide-containing molecules for conjugation or labeling applications. It is not approved for clinical use. Molecular formula: C15H18O3, molecular weight: 246.3. It is a fatty acid analog. Synonyms: 6-(2-Propargyloxyphenyl)hexanoic acid. Solubility: soluble in DMSO, ethanol. Storage: store at -20degC. Purity: ≥98% (by NMR and TLC). References: PPOH is described as an inhibitor of CYP epoxidase and cyclooxygenase activity. |
| Molecular Formula |
C15H18O3
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|---|---|
| Molecular Weight |
246.30
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| Exact Mass |
246.125
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| CAS # |
206052-01-9
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| PubChem CID |
53741002
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
411.0±40.0 °C at 760 mmHg
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| Flash Point |
151.1±20.8 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.534
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| LogP |
3.05
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
18
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| Complexity |
289
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C#CCOC1=CC=CC=C1CCCCCC(=O)O
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| InChi Key |
CUNYTKVXYZYERK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H18O3/c1-2-12-18-14-10-7-6-9-13(14)8-4-3-5-11-15(16)17/h1,6-7,9-10H,3-5,8,11-12H2,(H,16,17)
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| Chemical Name |
6-(2-prop-2-ynoxyphenyl)hexanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (406.01 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0601 mL | 20.3004 mL | 40.6009 mL | |
| 5 mM | 0.8120 mL | 4.0601 mL | 8.1202 mL | |
| 10 mM | 0.4060 mL | 2.0300 mL | 4.0601 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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